Methyl iodide → 4-Chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

Participants

Reaction Steps

To a stirred solution of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (27) (J. Org. Chem., 2001, 66, 17, 5723-5730) (643 mg, 4.15 mmol) in DMF (41 mL) was added NaH (60% in mineral oil, 330 mg, 8.3 mmol) in one portion at 0° C. and the mixture was stirred for 1 h followed by addition of methyl iodide (0.28 mL, 4.5 mmol). The reaction mixture was allowed to warm up to the room temperature, stirred for an additional hour and quenched with AcOH (1 mL) to form a suspension which was stirred for 10 min and concentrated under reduced pressure to give a solid. This material was dissolved in AcOEt, the solution was washed with cold saturated NaHCO3 solution and water, dried over Na2SO4, and concentrated to produce the title compound 28 as a pale yellow solid (640 mg, 93% yield). 1H NMR (400 MHz, CD3OD) δ(ppm): 8.51 (s, 1H), 7.75 (d, J=3.3 Hz, 1H), 6.62 (d, J=3.3 Hz, 2H), 4.15 (s, 1H). LRMS (M+1) 168.1 (100%), 170.1 (34%).

Provenance & Evidence